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Search results; Over 1,000 places in Leeward Settlement

Guest favorite
Condo in Leeward Settlement
New! Luxury 1Bed Large Condo
1 bed
May 5 – 10
4.95 out of 5 average rating, 40 reviews
Superhost
Home in Leeward Settlement
💦 LIQUID 💦 LUXURY Villa 🖤 on the WATER !!!💙
5 beds
May 26 – 31
4.91 out of 5 average rating, 90 reviews
Guest favorite
Villa in Providenciales
Amazing Waterfront Villa on Leeward Canals
7 beds
May 6 – 11
5.0 out of 5 average rating, 39 reviews
Home in Caicos Islands
! ! NEW ! ! Designers Dream Marina's Beach House
7 beds
Apr 29 – May 4
4.85 out of 5 average rating, 13 reviews
Guest favorite
Villa in Leeward Settlement
Ocean Pearl-Brand new villa/pool in governors road
3 beds
Apr 21 – 26
4.93 out of 5 average rating, 15 reviews
Villa in Leeward Settlement
Live style villa
4 beds
Apr 21 – 26
Superhost
Home in Providenciales
Newly Listed 2BR Canal Front
2 beds
Apr 22 – 27
New place to stay
Guest favorite
Apartment in Leeward Settlement
Leisure in Paradise
May 1 – 6
4.95 out of 5 average rating, 231 reviews
Superhost
Cottage in Providenciales, Turks and Caicos Islands
Welcome to Artemis Retreat!
3 beds
May 10 – 15
4.87 out of 5 average rating, 90 reviews
Guest favorite
Home in Leeward Settlement
PERIWINKLE | Charming Island Home|Near to Beach
2 beds
May 19 – 24
4.95 out of 5 average rating, 60 reviews
Guest favorite
Villa in Leeward Settlement
Providenciales Beach Front Villa
3 beds
Aug 19 – 24
4.93 out of 5 average rating, 57 reviews
Guest favorite
Villa in Leeward Settlement
Perroquet | Family Villa near Leeward Beach
3 beds
Jun 8 – 13
5.0 out of 5 average rating, 29 reviews
Guest favorite
Villa in Leeward Settlement
Byculla Villa
4 king beds
Apr 28 – May 3
4.94 out of 5 average rating, 33 reviews
Superhost
Villa in Providenciales
Leeward Jewel Villa | 7 Bedrooms | Waterfront Vi
8 beds
Jul 15 – 20
4.86 out of 5 average rating, 14 reviews
Guest favorite
Home in Leeward Settlement
Vision Balance - Canal Front Home in Leeward
6 beds
Apr 21 – 26
5.0 out of 5 average rating, 24 reviews
Villa in Leeward Settlement
YOLO - Never second guess a vacation worth taking
6 beds
Apr 30 – May 5
Guest favorite
Villa in Grace Bay
Calico Villa
3 beds
Jun 8 – 13
4.96 out of 5 average rating, 85 reviews
Villa in Leeward Settlement
Caribbean Escape Luxe Waterfront Villa with Pool
9 beds
Jun 6 – 11